N-(2,6-Dimethyl­phen­yl)-4-methyl­benzamide

Gowda, B.T.; Tokarčík, M.; Kožíšek, J.; Sowmya, B.P.; Fuess, H.

doi:10.1107/S1600536809022648

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1612

doi:10.1107/S1600536809022648

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N-(2,6-Dimethylphenyl)-4-methylbenzamide

B. Thimme Gowda,^a ^* Miroslav Tokarčík,^b Jozef Kožíšek,^b B. P. Sowmya ^a and Hartmut Fuess ^c

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bFaculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and ^cInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 3 June 2009; accepted 12 June 2009; online 17 June 2009)

In the molecular structure of the title compound, C₁₆H₁₇NO, the two aromatic rings are close to orthogonal to each other [dihedral angle 78.8 (1)°], while the central –NH—C(=O)– amide core is nearly coplanar with the benzoyl ring, forming a dihedral angle of 3.5 (2)°. Intermolecular N—H⋯O hydrogen bonds in the crystal structure link the molecules into infinite chains running along the c axis of the crystal, and a C—H⋯O interaction also occurs.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ). For related structures, see: Gowda, Foro et al. (2008 , 2009 ); Gowda, Tokarčík et al. (2008 ).

Experimental

Crystal data

C₁₆H₁₇NO
M_r = 239.31
Tetragonal, I 4₁ /a
a = 16.6224 (5) Å
c = 19.9508 (7) Å
V = 5512.5 (3) Å³
Z = 16
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 295 K
0.48 × 0.07 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.977, T_max = 0.992
17659 measured reflections
2649 independent reflections
1250 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.108
S = 0.99
2649 reflections
169 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.09 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.892 (13)	2.025 (14)	2.8814 (16)	160.6 (15)
C7—H7⋯O1ⁱ	0.93	2.48	3.385 (2)	165
Symmetry code: (i) $[y-{\script{1\over 4}}, -x+{\script{3\over 4}}, z-{\script{1\over 4}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2002 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022648/dn2462sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022648/dn2462Isup2.hkl

checkCIF report

Comment top

As part of a study of the substituent effects on the crystal structures of benzanilides (Gowda, Foro et al., 2008, 2009; Gowda, Tokarčík et al., 2008), in the present work, the structure of 4-methyl-N-(2,6-dimethylphenyl)benzamide (I) has been determined. The conformations of the N—H and C═O bonds in the amide segment of the structure are anti to each other (Fig.1), similar to that observed in 4-methyl-N-(phenyl)benzamide (Gowda, Foro et al., 2009), N-(2,6-dimethylphenyl)benzamide (Gowda, Tokarčík et al., 2008), 2-methyl-N-(2,6-dimethylphenyl)benzamide (Gowda, Foro et al., 2008) and other benzanilides, with similar bond parameters. The two aromatic rings in the structure of (I) make the dihedral angle of 78.8 (1)°, while the central amide core –NH—C(═O)– is nearly coplanar with the benzoyl ring, forming a dihedral angle of 3.5 (2)°. Part of the crystal structure of (I), showing the formation of hydrogen-bonded chains (Table 1) running in [001] direction is shown in Fig.2.

Related literature top

For preparation of the title compound, see: Gowda et al. (2003). For related structures, see: Gowda, Foro et al. (2008, 2009); Gowda, Tokarčík et al. (2008).

Experimental top

The title compound was prepared according to the method described by Gowda et al. (2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Needle-like colourless single crystals of the title compound were obtained by slow evaporation from an ethanol solution of the compound (0.5 g in about 30 ml of ethanol) at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of (I) showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure of (I), showing the formation of hydrogen-bonded chains running in [001] direction. Symmetry code (i): y - 1/4, -x + 3/4, z - 1/4. H atoms not involved in hydrogen bonding have been omitted.

N-(2,6-Dimethylphenyl)-4-methylbenzamide top

Crystal data top

C₁₆H₁₇NO	D_x = 1.153 Mg m⁻³
M_r = 239.31	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 3736 reflections
Hall symbol: -I 4ad	θ = 3.2–29.6°
a = 16.6224 (5) Å	µ = 0.07 mm⁻¹
c = 19.9508 (7) Å	T = 295 K
V = 5512.5 (3) Å³	Needle, colourless
Z = 16	0.48 × 0.07 × 0.07 mm
F(000) = 2048

Data collection top

Oxford Diffraction Xcalibur diffractometer	2649 independent reflections
Graphite monochromator	1250 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm^-1	R_int = 0.039
ω scans with κ offsets	θ_max = 25.8°, θ_min = 3.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	h = −19→20
T_min = 0.977, T_max = 0.992	k = −18→20
17659 measured reflections	l = −24→24

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = [exp(2.10(sinθ/λ)²)]/[σ²(F_o²) + (0.0579P)²], where P = 0.33333F_o² + 0.66667F_c²
2649 reflections	(Δ/σ)_max < 0.001
169 parameters	Δρ_max = 0.09 e Å⁻³
2 restraints	Δρ_min = −0.12 e Å⁻³

Crystal data top

C₁₆H₁₇NO	Z = 16
M_r = 239.31	Mo Kα radiation
Tetragonal, I4₁/a	µ = 0.07 mm⁻¹
a = 16.6224 (5) Å	T = 295 K
c = 19.9508 (7) Å	0.48 × 0.07 × 0.07 mm
V = 5512.5 (3) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer	2649 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	1250 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.992	R_int = 0.039
17659 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	2 restraints
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.09 e Å⁻³
2649 reflections	Δρ_min = −0.12 e Å⁻³
169 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.27487 (9)	0.49299 (9)	0.25025 (7)	0.0506 (4)
O1	0.26537 (8)	0.52765 (7)	0.30418 (5)	0.0697 (4)
N1	0.25165 (9)	0.52730 (8)	0.19248 (6)	0.0573 (4)
H1N	0.2648 (10)	0.5037 (9)	0.1539 (7)	0.069*
C2	0.31055 (9)	0.41089 (9)	0.24642 (6)	0.0483 (4)
C3	0.33373 (14)	0.37365 (12)	0.30424 (8)	0.0900 (7)
H3	0.3289	0.4009	0.3448	0.108*
C4	0.36405 (15)	0.29691 (13)	0.30384 (9)	0.0959 (7)
H4	0.3789	0.2735	0.3443	0.115*
C5	0.37308 (10)	0.25407 (10)	0.24670 (9)	0.0606 (5)
C6	0.34988 (13)	0.29146 (12)	0.18953 (9)	0.0828 (6)
H6	0.3548	0.264	0.1491	0.099*
C7	0.31947 (13)	0.36797 (11)	0.18884 (8)	0.0769 (6)
H7	0.3046	0.3911	0.1482	0.092*
C8	0.21647 (11)	0.60581 (10)	0.18922 (7)	0.0565 (4)
C9	0.13575 (12)	0.61467 (10)	0.20521 (7)	0.0630 (5)
C10	0.10337 (13)	0.69090 (13)	0.20139 (10)	0.0801 (6)
H10	0.0496	0.6988	0.2125	0.096*
C11	0.14898 (17)	0.75510 (13)	0.18149 (11)	0.0937 (7)
H11	0.126	0.806	0.1793	0.112*
C12	0.22797 (16)	0.74490 (12)	0.16481 (10)	0.0885 (7)
H12	0.2579	0.7889	0.1505	0.106*
C13	0.26422 (12)	0.66992 (11)	0.16895 (9)	0.0700 (5)
C14	0.40544 (13)	0.16975 (11)	0.24629 (11)	0.0866 (6)
H14A	0.3916	0.1441	0.2047	0.13*	0.5
H14B	0.3825	0.1401	0.2829	0.13*	0.5
H14C	0.4629	0.1711	0.251	0.13*	0.5
H14D	0.4331	0.1594	0.2877	0.13*	0.5
H14E	0.4422	0.1635	0.2095	0.13*	0.5
H14F	0.3618	0.1324	0.2414	0.13*	0.5
C15	0.08424 (12)	0.54478 (13)	0.22548 (10)	0.0842 (6)
H15A	0.0822	0.5064	0.1895	0.126*
H15B	0.0309	0.5634	0.2353	0.126*
H15C	0.1067	0.5197	0.2646	0.126*
C16	0.35125 (14)	0.65809 (14)	0.15300 (11)	0.0971 (7)
H16A	0.3778	0.6338	0.1906	0.146*
H16B	0.3756	0.7092	0.1435	0.146*
H16C	0.3563	0.6237	0.1146	0.146*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0587 (10)	0.0565 (10)	0.0367 (8)	0.0018 (8)	0.0004 (7)	0.0000 (7)
O1	0.1009 (10)	0.0724 (8)	0.0358 (6)	0.0166 (7)	−0.0008 (5)	−0.0073 (5)
N1	0.0802 (10)	0.0571 (9)	0.0347 (6)	0.0149 (7)	−0.0026 (6)	−0.0030 (6)
C2	0.0532 (9)	0.0524 (10)	0.0391 (8)	0.0019 (8)	0.0000 (7)	0.0014 (7)
C3	0.144 (2)	0.0805 (15)	0.0451 (10)	0.0401 (14)	−0.0106 (11)	0.0004 (9)
C4	0.149 (2)	0.0801 (15)	0.0588 (12)	0.0407 (15)	−0.0138 (12)	0.0123 (10)
C5	0.0590 (11)	0.0547 (11)	0.0681 (11)	0.0028 (8)	0.0006 (8)	0.0053 (9)
C6	0.1222 (18)	0.0660 (14)	0.0603 (11)	0.0237 (12)	−0.0004 (11)	−0.0090 (9)
C7	0.1186 (17)	0.0670 (13)	0.0450 (9)	0.0233 (11)	−0.0040 (10)	0.0010 (8)
C8	0.0777 (13)	0.0525 (11)	0.0392 (8)	0.0119 (10)	−0.0078 (8)	−0.0030 (7)
C9	0.0758 (14)	0.0587 (12)	0.0546 (10)	0.0104 (10)	−0.0076 (8)	−0.0021 (8)
C10	0.0811 (14)	0.0717 (15)	0.0874 (13)	0.0192 (12)	−0.0078 (11)	−0.0007 (11)
C11	0.116 (2)	0.0634 (15)	0.1019 (16)	0.0252 (15)	−0.0078 (14)	0.0029 (11)
C12	0.116 (2)	0.0550 (13)	0.0946 (14)	−0.0017 (13)	0.0019 (13)	0.0062 (10)
C13	0.0870 (15)	0.0604 (13)	0.0625 (10)	0.0017 (11)	−0.0007 (9)	−0.0021 (9)
C14	0.0941 (16)	0.0622 (13)	0.1034 (15)	0.0131 (11)	−0.0005 (12)	0.0093 (11)
C15	0.0811 (15)	0.0787 (14)	0.0928 (14)	0.0011 (12)	0.0017 (11)	0.0046 (10)
C16	0.0926 (17)	0.0928 (16)	0.1059 (16)	−0.0052 (13)	0.0143 (13)	−0.0034 (12)

Geometric parameters (Å, º) top

C1—O1	1.2307 (16)	C10—C11	1.368 (3)
C1—N1	1.3427 (17)	C10—H10	0.93
C1—C2	1.490 (2)	C11—C12	1.365 (3)
N1—C8	1.431 (2)	C11—H11	0.93
N1—H1N	0.892 (13)	C12—C13	1.387 (3)
C2—C7	1.360 (2)	C12—H12	0.93
C2—C3	1.365 (2)	C13—C16	1.494 (3)
C3—C4	1.372 (3)	C14—H14A	0.96
C3—H3	0.93	C14—H14B	0.96
C4—C5	1.352 (2)	C14—H14C	0.96
C4—H4	0.93	C14—H14D	0.96
C5—C6	1.355 (2)	C14—H14E	0.96
C5—C14	1.501 (2)	C14—H14F	0.96
C6—C7	1.369 (3)	C15—H15A	0.96
C6—H6	0.93	C15—H15B	0.96
C7—H7	0.93	C15—H15C	0.96
C8—C9	1.387 (2)	C16—H16A	0.96
C8—C13	1.389 (2)	C16—H16B	0.96
C9—C10	1.379 (2)	C16—H16C	0.96
C9—C15	1.499 (3)

O1—C1—N1	120.98 (15)	C13—C12—H12	119.5
O1—C1—C2	121.65 (13)	C12—C13—C8	117.29 (19)
N1—C1—C2	117.35 (13)	C12—C13—C16	121.75 (19)
C1—N1—C8	122.94 (12)	C8—C13—C16	120.95 (18)
C1—N1—H1N	119.0 (11)	C5—C14—H14A	109.5
C8—N1—H1N	117.5 (10)	C5—C14—H14B	109.5
C7—C2—C3	116.44 (15)	H14A—C14—H14B	109.5
C7—C2—C1	124.54 (14)	C5—C14—H14C	109.5
C3—C2—C1	118.98 (14)	H14A—C14—H14C	109.5
C2—C3—C4	121.38 (16)	H14B—C14—H14C	109.5
C2—C3—H3	119.3	C5—C14—H14D	109.5
C4—C3—H3	119.3	H14A—C14—H14D	141.1
C5—C4—C3	122.37 (17)	H14B—C14—H14D	56.3
C5—C4—H4	118.8	H14C—C14—H14D	56.3
C3—C4—H4	118.8	C5—C14—H14E	109.5
C4—C5—C6	115.88 (16)	H14A—C14—H14E	56.3
C4—C5—C14	122.41 (17)	H14B—C14—H14E	141.1
C6—C5—C14	121.70 (17)	H14C—C14—H14E	56.3
C5—C6—C7	122.67 (16)	H14D—C14—H14E	109.5
C5—C6—H6	118.7	C5—C14—H14F	109.5
C7—C6—H6	118.7	H14A—C14—H14F	56.3
C2—C7—C6	121.27 (15)	H14B—C14—H14F	56.3
C2—C7—H7	119.4	H14C—C14—H14F	141.1
C6—C7—H7	119.4	H14D—C14—H14F	109.5
C9—C8—C13	122.57 (16)	H14E—C14—H14F	109.5
C9—C8—N1	118.78 (16)	C9—C15—H15A	109.5
C13—C8—N1	118.63 (17)	C9—C15—H15B	109.5
C10—C9—C8	117.55 (18)	H15A—C15—H15B	109.5
C10—C9—C15	120.28 (19)	C9—C15—H15C	109.5
C8—C9—C15	122.17 (16)	H15A—C15—H15C	109.5
C11—C10—C9	121.1 (2)	H15B—C15—H15C	109.5
C11—C10—H10	119.4	C13—C16—H16A	109.5
C9—C10—H10	119.4	C13—C16—H16B	109.5
C12—C11—C10	120.47 (19)	H16A—C16—H16B	109.5
C12—C11—H11	119.8	C13—C16—H16C	109.5
C10—C11—H11	119.8	H16A—C16—H16C	109.5
C11—C12—C13	121.0 (2)	H16B—C16—H16C	109.5
C11—C12—H12	119.5

O1—C1—N1—C8	1.4 (3)	C1—N1—C8—C9	−79.3 (2)
C2—C1—N1—C8	179.93 (15)	C1—N1—C8—C13	101.84 (18)
O1—C1—C2—C7	177.04 (17)	C13—C8—C9—C10	−1.0 (2)
N1—C1—C2—C7	−1.5 (3)	N1—C8—C9—C10	−179.76 (14)
O1—C1—C2—C3	−0.5 (3)	C13—C8—C9—C15	178.53 (16)
N1—C1—C2—C3	−179.03 (17)	N1—C8—C9—C15	−0.2 (2)
C7—C2—C3—C4	−0.2 (3)	C8—C9—C10—C11	1.0 (3)
C1—C2—C3—C4	177.5 (2)	C15—C9—C10—C11	−178.47 (18)
C2—C3—C4—C5	0.3 (4)	C9—C10—C11—C12	0.1 (3)
C3—C4—C5—C6	−0.3 (3)	C10—C11—C12—C13	−1.4 (3)
C3—C4—C5—C14	−179.3 (2)	C11—C12—C13—C8	1.4 (3)
C4—C5—C6—C7	0.3 (3)	C11—C12—C13—C16	−178.01 (19)
C14—C5—C6—C7	179.3 (2)	C9—C8—C13—C12	−0.2 (2)
C3—C2—C7—C6	0.2 (3)	N1—C8—C13—C12	178.56 (15)
C1—C2—C7—C6	−177.35 (18)	C9—C8—C13—C16	179.20 (15)
C5—C6—C7—C2	−0.3 (3)	N1—C8—C13—C16	−2.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.89 (1)	2.03 (1)	2.8814 (16)	161 (2)
C7—H7···O1ⁱ	0.93	2.48	3.385 (2)	165

Symmetry code: (i) y−1/4, −x+3/4, z−1/4.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇NO
M_r	239.31
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	295
a, c (Å)	16.6224 (5), 19.9508 (7)
V (Å³)	5512.5 (3)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.48 × 0.07 × 0.07

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.977, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	17659, 2649, 1250
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.612

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.108, 0.99
No. of reflections	2649
No. of parameters	169
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.09, −0.12

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.892 (13)	2.025 (14)	2.8814 (16)	160.6 (15)
C7—H7···O1ⁱ	0.93	2.48	3.385 (2)	165

Symmetry code: (i) y−1/4, −x+3/4, z−1/4.

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for an extension of his research fellowship. MT and JK thank the Grant Agency of the Slovak Republic (VEGA 1/0817/08) and Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

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